Synthesis and biological evaluation of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepine and its cycloalkane and cycloalkene condensed analogues
El Haimer, M., Palkó, M., Haukka, M., Gajdács, M., Zupkó, I., & Fülöp, F. (2021). Synthesis and biological evaluation of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepine and its cycloalkane and cycloalkene condensed analogues. RSC Advances, 11, 6952-6957. https://doi.org/10.1039/d0ra10553h
Published inRSC Advances
DisciplineEpäorgaaninen ja analyyttinen kemiaEpäorgaaninen kemiaInorganic and Analytical ChemistryInorganic Chemistry
© 2021 The Author(s). Published by the Royal Society of Chemistry
Derivatives of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepinone and its cycloalkane and cycloalkene condensed analogues have been conveniently synthesized through a three-step reaction sequence. An atom-economical, one-pot, three-step cascade process engaging five reactive centers (amide, amine, carbonyl, azide, and alkyne) has been performed for the synthesis of alicyclic derivatives of quinazolinotriazolobenzodiazepine using cyclohexane, cyclohexene, and norbornene β-amino amides. The stereochemistry and relative configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy and X-ray crystallography. The reaction was also performed using enantiomeric starting materials leading to enantiomeric quinazolinotriazolobenzodiazepine with an ee of 95%. The synthesis of 9H-benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepinone, a new heterocyclic system, was achieved in a good yield using a retro Diels–Alder (RDA) procedure. Some compounds were tested for antiproliferative activities against five human cancer cell lines of gynecological. ...
PublisherRoyal Society of Chemistry (RSC)
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Additional information about fundingWe are grateful to the Hungarian Research Foundation (OTKA No. K 115731). The financial support of the GINOP-2.3.2-15-2016-00038 project is acknowledged. The Ministry of Human Capacities, Hungary grant, TKP-2020 is acknowledged. M. G. was supported by the János Bolyai Research Scholarship (BO/00144/20/5) of the Hungarian Academy of Sciences, the New National Excellence Programme (ÚNKP-20-5-SZTE-330) of the Ministry of Human Resources, and ESCMID's “30 under 30” Award. ...
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